SO, it's about time I get back to you. I hope I am in time...
If you would like to do a wine tour in the Chianti Classico area which includes a visit to an olive oil mill, I would recommend that you contact Castello di Volpaia (www.volpaia.it) for a tour & tasting. The village is absolutely stunning and you could combine with a meal in the village.
Other wineries also do organized tours of their cellers in English, as for example Dievole (www.dievole.it) , or Ricasoli (www.ricasoli.it), or if you would like to see a smaller winery Casa Emma (www.casaemma.com).
If you are interested in attending an olive oil lecture at an olive mill, please email me and I will help you set it up.
I hope this helps!